Tosh.0 star Daniel Tosh has recently come under fire for a controversial routine about rape at Los Angeles’ Laugh Factory, but the incident wasn’t the comic’s first time trying to make light of a serious subject.

After an outspoken audience member vocalized their disdain for the material at his July 6th show, Tosh reportedly replied “Wouldn’t it be funny if that girl got raped by like, 5 guys right now? Like right now?”

Though critics have taken aim at Tosh for this particular joke, many fans jumped to his defense and noted that the 37-year-old comic’s career has been riddled with zingers taking aim at religion, sex, women, and — again — rape.

So is Tosh’s material funny, or did he really take it too far with the heckler? Launch the gallery to read more of comics past controversial quotes.

However, Tosh’s jokes about controversial subjects aren’t just limited to his stand-up sets, but also his own show on Comedy Central.

In a 2011 episode of Tosh.0, which actually drew the highest ratings of any cable show that night, Tosh makes a knife rape joke based on gory footage of Libyan leader Muammar Qaddafi’s murder — retooling it to be prank dubbed “Qaddafi’d.”

Fellow comedians were quick to jump into Tosh’s defense when he received backlash for his remarks.

“It’s a comedy show and it’s Daniel Tosh — you’re going to laugh and be offended at times, comes with the territory,” saidIliza Schlesinger, a regular headliner at West Hollywood’s Laugh Factory.

“You think Daniel doesn’t know rape is horrible? Most of comedy is based on something horrible,” Schlesinger told Celebuzz. “When that woman heckled him from the audience, the joke became less about rape and more about silencing an audience member who dared challenge him — something no comic would back down from. Rape isn’t funny. But, neither is heckling a comic.”

Since then, Tosh apologized for the joke, writing on his Twitter:

all the out of context misquotes aside, i’d like to sincerely apologize j.mp/PJ8bNs